Bismuth triflate catalyzed Claisen rearrangement of allyl naphthyl ethers

被引:53
作者
Ollevier, Thierry [1 ]
Mwene-Mbeja, Topwe M. [1 ]
机构
[1] Univ Laval, Dept Chim, Ste Foy, PQ G1K 7P4, Canada
基金
加拿大自然科学与工程研究理事会; 加拿大创新基金会;
关键词
bismuth; bismuth(III) triflate; Claisen; rearrangement; naphthol; green chemistry;
D O I
10.1016/j.tetlet.2006.03.193
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Bismuth triflate was found to be an efficient catalyst for the Claisen rearrangement of allyl naphthyl ethers. The reaction proceeds smoothly with a catalytic amount of bismuth triflate (20 mol %) to afford the corresponding ortho-allyl naphthol in moderate to good yields in most cases. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4051 / 4055
页数:5
相关论文
共 50 条
  • [31] Bismuth triflate-catalyzed mild and efficient epoxide opening by aromatic amines under aqueous conditions
    Ollevier, T
    Lavie-Compin, G
    TETRAHEDRON LETTERS, 2004, 45 (01) : 49 - 52
  • [32] Direct and Highly Diastereoselective Synthesis of Azaspirocycles by a Dysprosium(III) Triflate Catalyzed Aza-Piancatelli Rearrangement
    Palmer, Leoni I.
    de Alaniz, Javier Read
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (31) : 7167 - 7170
  • [33] Versatile Method for the Synthesis of 4-Aminocyclopentenones: Dysprosium(III) Triflate Catalyzed Aza-Piancatelli Rearrangement
    Veits, Gesine K.
    Wenz, Donald R.
    de Alaniz, Javier Read
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (49) : 9484 - 9487
  • [34] Silver Triflate Catalyzed Cyclopropyl Carbinol Rearrangement for Benzo[b]oxepine and 2H-Chromene Synthesis
    Chan, Philip Wai Hong
    Teo, Wan Teng
    Koh, Shaun Wei Yong
    Lee, Bo Ra
    Ayers, Benjamin James
    Ma, Dik-Lung
    Leung, Chung-Hang
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (20) : 4447 - 4456
  • [35] Asymmetric Synthesis of 3-Allyloxindoles and 3-Allenyloxindoles by Scandium(III)-Catalyzed Claisen Rearrangement Reactions
    Lai, Zeng-Wei
    Liu, Chuan
    Sun, Hongbin
    You, Shu-Li
    CHINESE JOURNAL OF CHEMISTRY, 2017, 35 (10) : 1512 - 1516
  • [36] Synthesis of Substituted Biaryls through Gold-Catalyzed Petasis-Ferrier Rearrangement of Propargyl Ethers
    Pati, Kamalkishore
    Alabugin, Igor V.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (19) : 3986 - 3990
  • [37] Environment-friendly organic synthesis using bismuth compounds.: Bismuth triflate catalyzed synthesis of substituted 3,4-dihydro-2H-1-benzopyrans
    Nguyen, MP
    Arnold, JN
    Peterson, KE
    Mohan, RS
    TETRAHEDRON LETTERS, 2004, 45 (51) : 9369 - 9371
  • [38] Room-Temperature Bismuth-Catalyzed Bis-arylation of Carbonyl Compounds with Aryl Ethers and Phenols
    Liu, Congrong
    Li, Manbo
    CHINESE JOURNAL OF CHEMISTRY, 2013, 31 (10) : 1274 - 1278
  • [39] Efficient microwave-assisted direct C-benzoylation of phenols and naphthols with benzoic acid catalyzed by bismuth triflate under solvent-free or ionic liquid conditions
    Phuong Hoang Tran
    Huy Quang Phung
    Minh Nhat Duong
    Nguyen-Nguyen Pham-Tran
    TETRAHEDRON LETTERS, 2017, 58 (16) : 1558 - 1563
  • [40] Indium triflate catalyzed rearrangement of aryl-substituted cyclopropyl carbinols to 1,4-disubstituted 1,3-butadienes
    Ranu, Brindaban C.
    Banerjee, Subhash
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (13) : 3012 - 3015